15 Of The Saddest Music Videos Ever Made

October 24, 2013  |  

Sometimes a director will create a music video so raw and emotional we can’t help but think “darn you” as we reach for tissues and wipe away tears after a three-to-five minute emotional roller coaster of a video. That’s precisely the reaction we had when it comes to the items in this list. Here are 15 of the saddest music videos ever made.

Aaron Hall Album Cover pf

Aaron Hall – “I Miss You”

Aaron Hall first started out with the group Guy, but after Teddy Riley decided to take his New Jack Swing to Blackstreet, Hall forged on with a solo career. His biggest hit by himself is the tender love song “I Miss You.” In the video, Hall is over the moon that his lady is expecting his child He showers her with love and affection but his world is turned upside down when she starts having complications from the pregnancy. He ruses her to the hospital but it’s too late.

Immature promo photo pf

Immature “Please Don’t Go”

Boy band Immature struck gold with their 1996 hit “Please Don’t Go.” The teenaged trio crooned about losing puppy love and the accompanying video followed lead singer Marques Houston courting for a young girl. They fall in love but little does he know, his girlfriend is terminally sick and she passes away. Singing barefoot in the rain and by her gravesite, a crying Houston sings for his girl and best friend to come back to him. For anyone who’s lost a love back in the day, the song and video brings back sweet yet bitter memories.

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WENN

R. Kelly – “If I Could Turn Back The Hands Of Time”

There’s no disputing that he can make lovemaking songs like the best of them, but R. Kelly also has a knack for writing songs that will touch other emotions. For the ballad “If I Could Turn Back The Hands Of Time,” the video showed what was and what could have been for a loving couple as the hands of time were actually turned backwards before the man, played by R. Kelly, was killed in a car crash. The video reminds us all to stop wasting time focusing on the negative things like fighting and arguing because it wastes precious time, a lesson we all could benefit from.

2Pac Dear Mama cover

2Pac – “Dear Mama”

If you ever want to see a thug’s softer side, ask him about his mother. He may have had “Thug Life” scrawled across his stomach and frequently walked around donning a bulletproof vest, but 2Pac decided to lift the veil and show the world his Achilles heel with the song “Dear Mama.” The video opens with his mother Afeni Shakur talking about how happy she was to give birth to a son. Images from the video included his mother watching actual footage of 2Pac while a lookalike was used for other scenes because the rapper was incarcerated at the time of the filming. The tribute to 2Pac’s mother is one of 25 songs that were added to the National Recording Registry in 2010. The Library of Congress has called “Dear Mama” “a moving and eloquent homage to both the murdered rapper’s own mother and all mothers struggling to maintain a family in the face of addiction, poverty and societal indifference.”

"R. Kelly pf"

WENN

R. Kelly “Down Low (Nobody has To Know)”

Although it technically isn’t a love song, and actually celebrated the virtues of keeping an affair a secret, the video for R. Kelly’s “Down Low” was a real tearjerker. Playing the right hand man to boss Mr. Biggs, the legendary Ron Isley, Kelly was entrusted to keep the boss’s wife company but not the type of company Kellz was providing. Actress Garcelle Beauvais played the woman in the middle. Once Mr. Biggs found out the truth on what was really going on behind his back, Kelly was lucky to roll away in a wheelchair with his life. Mrs. Biggs wasn’t so lucky…

Boyz II Men promo shot pf

Boyz II Men – “It’s So Hard To Say Goodbye To Yesterday”

Boyz II Men burst onto the music scene in the early 90’s rocking paisley ties and argyle sweater vests with their debut song “Motown Philly” but it was their second song that really showcased their singing skills. The quartet sang an acapella version of the 1975 song “It’s So Hard To Say Goodbye To Yesterday” from the cult classic film “Cooley High.” The mournful video followed the Philly foursome as they sung the beautifully depressing song throughout the gritty streets of the neighborhood and at a cemetery. The song would help to move nine million copies of their debut album CooleyHighHarmony.

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Bone Thugs N Harmony – “Tha Crossroads”

In the early 90’s, west coast group Bone Thugs N Harmony signed under Eazy E’s label and were ready to become rap superstars. After they released their debut album to little fanfare, they were shocked, like the rest of the world, to watch their mentor Eazy E pass away from AIDS. As part of their second album, the Cleveland,OH group released the song “Crossroads,” which paid tribute to the former N.W.A. member along and other lost loved ones, including Wish Bone’s Uncle Charles. The video followed the grim reaper walking around collecting the spirits of their loved ones before taking them to a mountaintop to receive wings. “Tha Crossroads” was the biggest hit for the group, who recently reunited at the 2013 BET Hip-Hop Awards.

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WENN

Marsha Ambrosius – “Far Away”

As one half of Floerty, we fell in love with Marsha Ambrosius’ silky soft voice. After the group broke up, Ambrosius continued on with her career flying solo and released her debut album in 2011, home to the song “Fly Away.” While the song could be about a woman missing a friend, boyfriend or family member, for the video Ambrosius opted to tackle the very tough subject of homosexuality and suicide. The video is about a gay Black man who chooses to follow his heart but he watches his friends and family turn his back on him. Unable to live with to live with the pain, he kills himself. A subject close to her heart, at the end of the video a crying Ambrosius revealed she lost a friend to suicide and urges us all to accept one another.

"Sean 'Diddy' Combs pf"

WENN

Diddy Ft Faith and 112 – “I’ll Be Missing You”

In March of 1997, the rap world lost a legend when Christopher “Biggie Smalls” Wallace was shot and killed while out in Los Angeles. Putting his sorrow into words and then eventually dance steps, Sean “Puff Daddy/Diddy” Combs penned a song for his friend. He recruited his other Bad Boy label mates, Faith Evans and 112, and used a sample of The Police’s “Every Breath You Take” for the Biggie tribute “I’ll be Missing You.” Shot in Sydney, Australia and directed by Hype Williams, Puffy roamed the lush green countryside on a motorcycle while reminiscing about his friend. The video helped move over nine million copies of the song. That is certainly one way to mourn for a friend.

Aaliyah Rock the Boat cover pf

Aaliyah – “Rock the Boat”

With a couple movies under her belt and a brand new album to promote, singer Aaliyah headed down to the Bahamas to shoot the video for the upbeat and sensual song “Rock The Boat.” Tragically, she would never make it back to the States. The R&B singer perished in a plane crash while leaving the island shortly after the video wrapped. That’s why it’s so harrowing to look at the video. Even though we see a happy and smiling Aayliah, we know these are the last few hours of her life. By the time the video ends, Aayilah drifts away in the water as if she’s assimilating her ascension to heaven. It’s hard to hold back the tears.

DRS Gangsa Lean cover pf

DRS – “Gangsta Lean”

Who knew that four thugged out guys rocking bandanas and denim outfits gripping 40 oz would have people wiping tears of sorrow from their eyes? DRS popped up on the music scene in 1993 with their popular song “Gangsta Lean.” While most people today would glance at the title and assume it’s another rap song about codeine in a cup, it was actually a moving tribute to fallen friends and loved ones. The term “gangsta lean” referred to low riding cars hooked up to hydraulics that would be able to dip and lean. The video was equally touching, even the customary pouring out some liquor “for those who aren’t here.” This would be the only hit song from the Sacramento, CA group.

"Toni Braxton pf"

WENN1

Toni Braxton – “Unbreak My Heart”

No other singer can do a heartbreaking ballad quite like Toni Braxton. Already a sad song about not being able to move on from a love lost, the accompanying video for “Unbreak My Heart” was beautifully tragic. Saying goodbye to her man, played by the very handsome Tyson Beckford, Toni waved as he peeled off on his motorcycle. A couple seconds later he was dead. Toni cried for her man throughout the video as she thought back to happier times of watching him do yoga shirtless or swim laps in the pool. We’d cry, too, if we lost a man who looked like Tyson and brushed our hair and washed our feet like that. Making things much worse is hearing the pleading in Braxton’s voice. By the end of the video, we all wished he could come back and unbreak her heart.

Boyz II Men End of the Road artwork

Boyz II Men – “End of the Road”

Boyz II Men were touring on the road while enjoying the success of their debut album “CooleyHighHarmony” when they took some time off to dip into the studio to record a song for Eddie Murphy’s film “Boomerang.” They reportedly knocked out the song in a couple hours but it would be one of the biggest hits in their career. The video followed the four boys from Philly around as they sang their hearts out on “End of the Road” but it was Michael McCary’s deep and baritone voice that melted butter and tugged at the heartstrings. The video helped the song sit at the top of the charts for a record-breaking 13 weeks in a row, shattering a record previously held by Elvis Presley.

Allure Album pf

Allure – “All Cried Out”

We have all been there: our bodies never knew such pleasure but our hearts never knew such pain. Allure tapped into the emotions of a woman scorned with their hit song “All Cried Out.” Joined by male group 112, Allure was finally done with the pain and tears and ready to move on. Though they pleaded for another chance, when the words “Apology not accepted, admit to the broken hearts you collected” were uttered, it was over. Becoming the anthem for every woman looking to move on in 1997, the group released a single in 2012, almost a decade after their last album.

Blackstreet album cover

Blackstreet – “Don’t Leave Me”

There’s something about a man pleading, “If you take your love away from me, I’ll go crazy. I’ll go insane.” Blackstreet did it best in their hit song “Don’t Leave Me.” Although the song was a bit uptempo, the foursome still managed to turn this song and an accompanying video as the song any man would play to win his love back. The video followed a broken-hearted man as he, and other men mourning a loss, used photos of his lady to try to build a tower to reach her in heaven. Too bad the group couldn’t stay together after a rift between original members Teddy Riley and Chauncey Hanniibal caused the group to split up. They now go by the name BS2 because Hannibal still owns the name to the original group.

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  • Brandon Roberts

    johnny cah hurt or three days grace never too late

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  • Maile00

    Good list! I can’t watch or listen to most of these songs! :’-(

  • PL

    madamenoire, i’m sorry, but the slideshows HAVE to stop. they’re glitchy, slow, and they’re annoying. please make an article option.

  • nani

    Brian McNight Back at 1

  • NachoAverage

    Hey.. What a about “Renee” by the Lost Boyz… sad af :’-(

  • gekajones1

    What about TLC’S Waterfalls or Sade’s No Ordinary Love?

  • Guest

    I thought Ne-yo’s Part of the List would be up there too. It was sad to me.

  • Tee Elyse

    Brenda’s Got A Baby was way more sad than Dear Mama to me! Good list tho… I was about five when that Aaron Hall video dropped and BOO HOOED like a baby!! Still shed tears to this day just listening to that song!

  • Shanice

    I still shed a tear at the “I Miss You” video by Aaron Hall. But where’s the Isley Brother video where Ron’s wife and daughter are killed by a drunk driver? That one really gets me

  • Suchalady

    This site is terribly annoying. Trying to watch any videos with ads and interviews playing on the side automatically grinds my gears. What a dumb idea.

  • PostmanLV

    and boyz II men sure as hell didn’t make it’s so hard to say goodbye

    • NachoAverage

      Sure didn’t. But this list is for videos mr. postman

  • nickibaby

    Where’s One Sweet Day? Good list tho, I can’t watch/listen to I Miss You without getting weepy.

  • Dawn

    What about Back at One By Bryan McKnight. They even had to stop showing the video after 9/11 because it hit too close to home for many.

    • Don’t drink the haterade.

      Oh God I remember that!

  • DatDude1

    idk how waterfalls aint on here

  • DatDude1

    I was a youngin when Aaron Hall dropped that video. That video messed up my whole day.

    • NachoAverage

      Lol… hellla!

  • thepreshest

    I also think the following are all sad: Aaliyah’s “I Miss You” especially w/ DMX speaking at the beginning, Musiq’s “Dontchange,” Dru Hill’s “Never Make a Promise” where the girl’s father is molesting her, and J. Cole’s “Crooked Smile”

    • HUgrad13

      I was thinking of dontchange the WHOLE time. Because I cry like a baby everytime I watch it

    • nickibaby

      Love by Musiq Soulchild is another one

  • fuzzydred

    Hold up, wait a minute! You’re telling me that you’re not going to give credit to Lisa Lisa & Cult Jam/Full Force for making the ORIGINAL “All Cried Out?” I was with you until I noticed that glaring oversight.

  • NachoAverage

    Bone is not a “West Coast” group… sorry 🙁

  • cellyb2000

    That damn gangsta lean gets to me every time!

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  • Dawniell Black

    How does 112/allures desecration of All Cried Out make this list instead of the original Lisa Lisa and Cult Jam with Full Force?

    • Maile00

      Remake is waaay better

      • Dawniell Black

        I don’t know how old you are but if you are under 30 I understand why you might think that I caught the tail end of the freestyle era and you had to be part of that time to understand it – but the 112/allure version just can’t compare. I had the Lisa Lisa vinyl and wore that song out.

  • Brit

    Eve’s “Love Is Blind” is also another sad one, always puts me into tears.

  • IAJS

    I miss you is the saddest video ever! If you don’t shed at least one tear during that video then you are a cold piece of work lol

  • Tiffany

    where’s 5 STEPS by Dru Hill? That one gets me sad everytime.

    • So True

      OMG!!! I was thinking of that one too. I cried EVERY time I saw that video. Brian McKnight “Everytime you go away” and Jodeci “Lately” are a couple other ones that come to mind but 5 Steps is top of that list. Great minds think alike!!!

      • Maile00

        Pretty much ANY B. McKnight song lol

  • lll

    RL “Good Man”

  • nathanhappenin

    missing you wasnt written by diddy it was written by sauce money

  • TC

    I TIP A FORRRTY TO YOUR MEMORY!!!!! Whooooo throwing it way back with the Gangsta Lean lol.
    I remember back in the day End of the Road was banned from being played in our house or car after it made my big bro break out in tears lol. And yup I still pick on him with that one haha.

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